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Chesapeake & Delmarva: 4-Day Plan You Can Actually Drive

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The 4-day version for June: every day fits real transit, opening hours and daylight. Prefer more or fewer days? 3-day plan · 4-day plan · best time to go.

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4
days
200 km
distance
6.5 h
driving
20
curated stops

💡 Good to know for this plan

Day 1 Annapolis

6 curated stops
Transit
0h30
Finish
~16:30
Temperature
18.5°C–27.6°C
Rainy days
~17
Daylight
14.7h
09:00
Maryland State House msa.maryland.gov read more map ↗
Explore the oldest legislative building in continuous use in the nation.
50 min · Annapolis · free
open: 9AM-5PM
10:00
William Paca House annapolis.org read more map ↗
Stroll through beautifully restored colonial gardens bursting with lush greenery.
50 min · Annapolis · $5 adult, $8-10 for guided tour
open: M-Sa 10AM-5PM, Su noon-5PM
11:00
Banneker-Douglass Museum bdmuseum.maryland.gov read more map ↗
Explore African American heritage through exhibits and artifacts in this historic museum.
50 min · Annapolis · Tu-Sa 10AM-4PM
open: Free, donations encouraged
12:00
Hammond-Harwood House hammondharwoodhouse.org read more map ↗
Admire elegant colonial architecture and period furnishings in this preserved mansion.
50 min · Annapolis · $10/adult, $5/child
open: Mar-Oct: Tu-Su noon-5PM, Nov-Feb: noon-4PM
13:00
The Hall of Presidents Before Washington presidentsbeforewashington.org map ↗
Discover early American leadership in a free, engaging exhibit near the waterfront.
50 min · Annapolis · Free
open: Open 24 hours a day, everyday
14:00
Maryland Hall for the Creative Arts marylandhall.org read more map ↗
Experience diverse performances and workshops in this vibrant arts center.
90 min · Annapolis
15:30
Chick & Ruth's chickandruths.com map ↗
Treat yourself to an enormous, legendary 6-pound shake that defines local indulgence.
60 min · Annapolis
open: Su-Tu 6:30AM-9PM, F-Sa 6:30AM-11PM
Overnight here
e.g. Hilton Garden Inn Annapolis · Annapolis Waterfront Hotel
Find a stay → Tours & tickets for the evening →

Day 2 Around Annapolis

4 curated stops
Transit
0h49
Finish
~15:35
Temperature
18.5°C–27.6°C
Rainy days
~17
Daylight
14.7h
09:00
Sandy Point State Park dnr.maryland.gov read more map ↗
Enjoy sweeping views of the Chesapeake Bay Bridge from sandy shores.
50 min · Annapolis · $4/person
11:00
Schooner Woodwind schoonerwoodwind.com map ↗
Feel the sea breeze and learn sailing traditions aboard a classic tall ship.
90 min · Annapolis · Adult $48, senior (60+) $46, child (age 11 and under) $31
open: Daily 11AM-6:30PM (April to October)
12:40
Historic Annapolis Museum & Store annapolis.org map ↗
Discover Maryland's layered history through dynamic, interactive exhibits.
50 min · Annapolis · free
open: M Tu Th 11AM-4PM, F-Su 11AM-5PM
13:45
U.S. Naval Academy Museum usna.edu
Engage with interactive displays showcasing naval history and heroic service.
50 min · Annapolis · free
open: M-Sa 9AM-5PM, Su 11AM-5PM
needs booking ahead: permit, timed entry or a guide details
14:35
Cantler's Riverside Inn cantlers.com map ↗
Savor authentic Maryland seafood served family-style on casual riverside benches.
60 min · Annapolis
Overnight here
e.g. Hilton Garden Inn Annapolis · Annapolis Waterfront Hotel
Find a stay → Tours & tickets for the evening →

Day 3 St. Michaels

3 curated stops
Transit
1h47
Finish
~15:05
Temperature
18.5°C–27.6°C
Rainy days
~17
Daylight
14.7h
10:25
Chesapeake Bay Maritime Museum cbmm.org read more
Explore historic boats and lighthouse exhibits showcasing the Bay's maritime heritage.
50 min · St. Michaels
11:30
St. Mary's Square Museum stmichaelsmuseum.org
Discover the town's history through engaging exhibits and walking tour options.
50 min · St. Michaels
open: May-Oct: M 10AM-1PM, F 1PM-4PM, Sa 10AM-4PM, Su 1PM-4PM; Nov-April by appointment only
12:35
Skipjack H.M. Krentz oystercatcher.com
Enjoy a scenic two-hour cruise on this traditional Chesapeake Bay workboat.
90 min · St. Michaels · $35/$18 children
open: 11AM, 2PM, ~5PM
14:05
The Crab Claw Restaurant thecrabclaw.com read more
Savor locally famous steamed crabs and a variety of fresh seafood dishes.
60 min · St. Michaels
Overnight here
e.g. Harbourtowne Golf Resort and Conferences Center · Five Gables Inn & Spa
Find a stay → Tours & tickets for the evening →

Day 4 Chincoteague & Assateague

4 curated stops
Transit
3h24
Finish
~17:50
Temperature
19.7°C–26.5°C
Rainy days
~15
Daylight
14.6h
11:50
Assateague Lighthouse read more map ↗
Explore bike trails and pony viewing spots along the wildlife refuge.
90 min · Chincoteague & Assateague
13:30
Wildlife Loop search map ↗
Cycle or hike through scenic paths with opportunities to spot wild ponies.
90 min · Chincoteague & Assateague
check access before you go details
15:10
Woodland Trail search map ↗
Enjoy easy bike rides and short hikes through the refuge's natural landscapes.
90 min · Chincoteague & Assateague
17:00
Wild Pony Auction chincoteague.com map ↗
Watch the spirited auction supporting the local volunteer fire company.
50 min · Chincoteague & Assateague
open: Starts at 8AM on the day after the Annual Pony Swim. Arrive early.

🚗 Rental cars for this trip →

🔍 Check before you book

Every stop is a real, sourced place, but opening hours change, roads close and businesses move. Check anything you're paying for before you book.

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